CA2491319A1 - Ophthalmic and otorhinolaryngological device materials - Google Patents
Ophthalmic and otorhinolaryngological device materials Download PDFInfo
- Publication number
- CA2491319A1 CA2491319A1 CA002491319A CA2491319A CA2491319A1 CA 2491319 A1 CA2491319 A1 CA 2491319A1 CA 002491319 A CA002491319 A CA 002491319A CA 2491319 A CA2491319 A CA 2491319A CA 2491319 A1 CA2491319 A1 CA 2491319A1
- Authority
- CA
- Canada
- Prior art keywords
- methacrylate
- acrylate
- cross
- formula
- polymeric material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/062—Polyethers
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials For Medical Uses (AREA)
- Prostheses (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Eyeglasses (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Polymerisation Methods In General (AREA)
- Graft Or Block Polymers (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
Disclosed are soft, high refractive index, acrylic device materials having improved strength. The materials contain cross-linked acrylate or methacrylate microspheres.
Claims (13)
1. A self-reinforced polymeric material comprising (a) a monofunctional acrylate or methacrylate monomer of formula (1), (b) a difunctional acrylate or methacrylate cross-linking monomer, and (c) a cross-linked acrylate or methacrylate microsphere of formula (2):
wherein:
A = H, CH3, CH2CH3, CH2OH;
B = (CH2)n, or [O(CH2)2]n;
D = (CH2)w;
m = 2-6;
n = 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, C n H2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w = 0-6, provided that m+w <=8; and E is H, C1 - C4 alkyl, C1 - C4 alkoxy, C6H5, CH2C6H5, or F, Cl, Br.
wherein:
A = H, CH3, CH2CH3, CH2OH;
B = (CH2)n, or [O(CH2)2]n;
D = (CH2)w;
m = 2-6;
n = 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, C n H2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w = 0-6, provided that m+w <=8; and E is H, C1 - C4 alkyl, C1 - C4 alkoxy, C6H5, CH2C6H5, or F, Cl, Br.
2. The polymeric material of Claim 1 wherein the material is made by radical polymerization of the monofunctional acrylate or methacrylate monomer of formula (1) and the difunctional acrylate or methacrylate cross-linking monomer in the presence of the cross-linked acrylate, or methacrylate microsphere of formula (2).
3. The polymeric material of Claim 1 wherein the difunctional acrylate or methacrylate cross-linking monomer (b) is selected from the group consisting of ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate;
CH2=C(CH3)C(O)O(CH2CH2O)n-C(O)C(CH3)=CH2 where n - 1 - 50;
CH2=C(CH3)C(O)O(CH2)t O-C(O)C(CH3)=CH2 where t= 3 - 20; and their corresponding acrylates.
CH2=C(CH3)C(O)O(CH2CH2O)n-C(O)C(CH3)=CH2 where n - 1 - 50;
CH2=C(CH3)C(O)O(CH2)t O-C(O)C(CH3)=CH2 where t= 3 - 20; and their corresponding acrylates.
4. The polymeric material of Claim 1 wherein the polymeric material comprises 75 - 98% (w/w) of the monofunctional acrylate or methacrylate monomer of formula (1), 0.1 - 5 % (w/w) of the difunctional acrylate of methacrylate cross-linking monomer, and 1 - 20 % (w/w) of the cross-linked acrylate or methacrylate microsphere of formula (2).
5. The polymeric material of Claim 4 wherein the polymeric material comprises 1 - 5 % (w/w) of the cross-linked acrylate or methacrylate microsphere of formula (2).
6. The polymeric material of Claim 1 wherein the material further comprises an ingredient selected from the group consisting of reactive UV
absorbers and reactive blue-light absorbers.
absorbers and reactive blue-light absorbers.
7. An ophthalmic or otorhinolaryngological device selected from the group consisting of intraocular lenses; contact lenses; keratoprostheses; corneal rings or inlays; otological ventilation tubes; and nasal implants, wherein the device comprises a self-reinforced polymeric material comprising (a) a monofunctional acrylate or methacrylate monomer of formula (1), (b) a difunctional acrylate or methacrylate cross-linking monomer, and (c) a cross-linked acrylate or methacrylate microsphere of formula (2):
wherein:
A = H, CH3, CH2CH3, CH2OH;
B = (CH2)m or [O(CH2)2]n;
D = (CH2)w;
m = 2-6;
n = 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, C n H2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w = 0-6, provided that m+w <= 8; and E is H, C1 - C4 alkyl, C1 - C4 alkoxy, C6H5, CH2C6H5, or F, Cl, Br.
wherein:
A = H, CH3, CH2CH3, CH2OH;
B = (CH2)m or [O(CH2)2]n;
D = (CH2)w;
m = 2-6;
n = 1-10;
Y is nothing, O, S, or NR, provided that if Y is O, S, or NR, then B is (CH2)m;
R is H, CH3, C n H2n+1 (n=1-10), iso-OC3H7, C6H5, or CH2C6H5;
w = 0-6, provided that m+w <= 8; and E is H, C1 - C4 alkyl, C1 - C4 alkoxy, C6H5, CH2C6H5, or F, Cl, Br.
8. The ophthalmic or otorhinolaryngological device of Claim 7 wherein the self-reinforced polymeric material is made by radical polymerization of the monofunctional acrylate or methacrylate monomer of formula (1) and the difunctional acrylate or methacrylate cross-linking monomer in the presence of the cross-linked acrylate, or methacrylate microsphere of formula (2).
9. The ophthalmic or otorhinolaryngological device of Claim 7 wherein the difunctional acrylate or methacrylate cross-linking monomer (b) is selected from the group consisting of ethylene glycol dimethacrylate; diethylene glycol dimethacrylate; allyl methacrylate; 1,3-propanediol dimethacrylate; 2,3-propanediol dimethacrylate; 1,6-hexanediol dimethacrylate; 1,4-butanediol dimethacrylate; CH2=C(CH3)C(O)O(CH2CH2O)n-C(O)C(CH3)=CH2 where n =
1 - 50; CH2=C(CH3)C(O)O(CH2)t O-C(O)C(CH3)=CH2 where t= 3 - 20; and their corresponding acrylates.
1 - 50; CH2=C(CH3)C(O)O(CH2)t O-C(O)C(CH3)=CH2 where t= 3 - 20; and their corresponding acrylates.
10. The ophthalmic or otorhinolaryngological device of Claim 7 wherein the self-reinforced polymeric material comprises 75 - 98% (w/w) of the monofunctional acrylate or methacrylate monomer of formula (1), 0.1 - 5 (w/w) of the difunctional acrylate of methacrylate cross-linking monomer, and 1 - 20 % (w/w) of the cross-linked acrylate or methacrylate microsphere of formula (2).
11. The ophthalmic or otorhinolaryngological device of Claim 10 wherein the self-reinforced polymeric material comprises 1 - 5 % (w/w) of the cross-linked acrylate or methacrylate microsphere of formula (2).
12. The ophthalmic or otorhinolaryngological device of Claim 11 wherein the self-reinforced polymeric material further comprises an ingredient selected from the group consisting of reactive UV absorbers and reactive blue-light absorbers.
13. The ophthalmic or otorhinolaryngological device of Claim 7 wherein the self-reinforced polymeric material comprises 65 - 70 % (w/w) of 2-phenylethyl acrylate, 25 - 33% (w/w) of 2-phenylethyl methacrylate, 1 - 4 % (w/w) of cross-linked 2-phenylethyl methacrylate microspheres having an average diameter 0.1 - 1 µm, and 0.5 -1.5 % (w/w) of a difunctional acrylate or methacrylate cross-linking monomer.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US39620102P | 2002-07-16 | 2002-07-16 | |
| US60/396,201 | 2002-07-16 | ||
| PCT/US2003/021902 WO2004007579A1 (en) | 2002-07-16 | 2003-07-15 | Ophthalmic and otorhinolaryngological device materials |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2491319A1 true CA2491319A1 (en) | 2004-01-22 |
| CA2491319C CA2491319C (en) | 2010-02-16 |
Family
ID=30115984
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2491319A Expired - Fee Related CA2491319C (en) | 2002-07-16 | 2003-07-15 | Ophthalmic and otorhinolaryngological device materials |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US6806337B2 (en) |
| EP (1) | EP1521786B1 (en) |
| JP (1) | JP4260742B2 (en) |
| AT (1) | ATE393175T1 (en) |
| AU (1) | AU2003249203B2 (en) |
| CA (1) | CA2491319C (en) |
| CY (1) | CY1107961T1 (en) |
| DE (1) | DE60320556T2 (en) |
| DK (1) | DK1521786T3 (en) |
| ES (1) | ES2301830T3 (en) |
| PT (1) | PT1521786E (en) |
| SI (1) | SI1521786T1 (en) |
| WO (1) | WO2004007579A1 (en) |
Families Citing this family (39)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| AU2003221129A1 (en) * | 2002-04-12 | 2003-10-27 | Menicon Co., Ltd. | Contact lens and production method for contact lens |
| CA2572935A1 (en) * | 2004-07-16 | 2006-02-23 | Alcon, Inc. | Ophthalmic and otorhinolaryngological device materials |
| US20060240096A1 (en) * | 2005-04-22 | 2006-10-26 | Kugler Chad J | Devices and methods for treating the gastrointestinal system |
| US8263721B2 (en) * | 2005-06-13 | 2012-09-11 | Novartis Ag | Ophthalmic and otorhinolaryngological device materials |
| ZA200710477B (en) * | 2005-06-13 | 2009-08-26 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials |
| DE602006013127D1 (en) * | 2005-06-13 | 2010-05-06 | Alcon Inc | MATERIALS FOR OPHTHALMIC AND OTORHINOLARYNGOLOGICAL DEVICES |
| TW200816966A (en) * | 2006-07-21 | 2008-04-16 | Alcon Mfg Ltd | Low-tack ophthalmic and otorhinolaryngological device materials |
| TWI399228B (en) * | 2006-07-21 | 2013-06-21 | Alcon Inc | Low-tack ophthalmic and otorhinolaryngological device materials |
| US8058323B2 (en) * | 2006-07-21 | 2011-11-15 | Novartis Ag | Low-tack ophthalmic and otorhinolaryngological device materials |
| US7714039B2 (en) * | 2006-07-21 | 2010-05-11 | Alcon, Inc. | Low-tack ophthalmic and otorhinolaryngological device materials |
| KR20090071628A (en) * | 2006-10-13 | 2009-07-01 | 알콘, 인코퍼레이티드 | Intraocular lenses with unique blue-violet cutoff and blue light transmission characteristics |
| ATE479664T1 (en) * | 2007-04-30 | 2010-09-15 | Alcon Inc | UV ABSORBER FOR GLASS LENS MATERIAL |
| EP2225325B1 (en) * | 2007-07-25 | 2011-06-01 | Alcon, Inc. | High refractive index ophthalmic device materials |
| TW200916531A (en) * | 2007-08-09 | 2009-04-16 | Alcon Inc | Ophthalmic lens materials containing chromophores that absorb both UV and short wavelength visible light |
| TWI435915B (en) * | 2007-08-09 | 2014-05-01 | Alcon Inc | Ophthalmic lens materials containing chromophores that absorb both uv and short wavelength visible light |
| TW200920330A (en) * | 2007-10-02 | 2009-05-16 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials containing an alkyl ethoxylate |
| TW200916130A (en) * | 2007-10-02 | 2009-04-16 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials containing an alkylphenol ethoxylate |
| TWI426931B (en) * | 2007-10-03 | 2014-02-21 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials |
| TWI461186B (en) * | 2007-10-05 | 2014-11-21 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials |
| TWI426932B (en) * | 2007-10-05 | 2014-02-21 | Alcon Inc | Ophthalmic and otorhinolaryngological device materials |
| WO2009102454A1 (en) * | 2008-02-12 | 2009-08-20 | Aaren Scientific Inc. | Ophthalmic lens having a yellow dye light blocking component |
| US7803359B1 (en) | 2008-05-06 | 2010-09-28 | Alcon, Inc. | UV-absorbers for ophthalmic lens materials |
| US7884228B1 (en) | 2008-05-06 | 2011-02-08 | Alcon, Inc. | UV-absorbers for ophthalmic lens materials |
| US8043607B2 (en) | 2008-07-15 | 2011-10-25 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
| US8236053B1 (en) | 2008-10-08 | 2012-08-07 | Novartis Ag | 2-amino benzophenone UV-absorbers for ophthalmic lens materials |
| TWI453199B (en) * | 2008-11-04 | 2014-09-21 | Alcon Inc | Uv/visible light absorbers for ophthalmic lens materials |
| US20100249273A1 (en) * | 2009-03-31 | 2010-09-30 | Scales Charles W | Polymeric articles comprising oxygen permeability enhancing particles |
| TWI487690B (en) | 2009-07-06 | 2015-06-11 | Alcon Inc | Visible light absorbers for ophthalmic lens materials |
| TWI464151B (en) | 2009-07-06 | 2014-12-11 | Alcon Inc | Uv/visible light absorbers for ophthalmic lens materials |
| TWI473629B (en) * | 2010-01-18 | 2015-02-21 | Alcon Inc | Visible light absorbers for ophthalmic lens materials |
| AU2011245400B2 (en) | 2010-04-29 | 2015-01-29 | Alcon Inc. | Intraocular lenses with combinations of UV absorbers and blue light chromophores |
| US8362177B1 (en) | 2010-05-05 | 2013-01-29 | Novartis Ag | High refractive index ophthalmic device materials with reduced tack |
| TW201311621A (en) | 2011-08-15 | 2013-03-16 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
| US8585938B1 (en) | 2012-03-30 | 2013-11-19 | Novartis Ag | UV-absorbers for ophthalmic lens materials |
| CN104395387A (en) | 2012-06-26 | 2015-03-04 | 诺华股份有限公司 | 2-amino benzophenone UV-absorbers for ophthalmic lens materials |
| JP6166479B2 (en) | 2013-12-04 | 2017-07-19 | ノバルティス アーゲー | Soft acrylic material with high refractive index and minimal greasing |
| WO2016100188A1 (en) | 2014-12-16 | 2016-06-23 | Novartis Ag | Hydrophobic acrylate-acrylamide copolymers for ophthalmic devices |
| ES2900002T3 (en) | 2014-12-16 | 2022-03-15 | Alcon Inc | Acrylate-acrylamide copolymers with low water content for ophthalmic devices |
| ES2703566T3 (en) | 2015-02-16 | 2019-03-11 | Novartis Ag | Wet packaging of intraocular lens materials with high refractive index |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3267084A (en) * | 1962-05-23 | 1966-08-16 | Gulf Oil Corp | Polymerizable 5-alkylene-m-dioxanyl acrylic esters |
| NL127481C (en) * | 1965-07-07 | 1900-01-01 | ||
| US4138383A (en) * | 1975-11-24 | 1979-02-06 | California Institute Of Technology | Preparation of small bio-compatible microspheres |
| ATE143677T1 (en) | 1990-11-07 | 1996-10-15 | Nestle Sa | POLYMERS AND THEIR USE FOR OPTHALMIC LENSES |
| US5290892A (en) * | 1990-11-07 | 1994-03-01 | Nestle S.A. | Flexible intraocular lenses made from high refractive index polymers |
| US5331073A (en) * | 1992-11-09 | 1994-07-19 | Allergan, Inc. | Polymeric compositions and intraocular lenses made from same |
| US5470932A (en) * | 1993-10-18 | 1995-11-28 | Alcon Laboratories, Inc. | Polymerizable yellow dyes and their use in opthalmic lenses |
| WO1996040303A1 (en) * | 1995-06-07 | 1996-12-19 | Alcon Laboratories, Inc. | Improved high refractive index ophthalmic lens materials |
| US5708094A (en) * | 1996-12-17 | 1998-01-13 | Bausch & Lomb Incorporated | Polybutadiene-based compositions for contact lenses |
| EP1210381A1 (en) | 1999-09-07 | 2002-06-05 | Alcon Universal, Ltd. | Ophthalmic and otorhinolaryngological device materials |
| WO2001018078A1 (en) * | 1999-09-07 | 2001-03-15 | Alcon Universal Ltd. | Foldable ophthalmic and otorhinolaryngological device materials |
| EP1178092A1 (en) * | 2000-08-01 | 2002-02-06 | Sika AG, vorm. Kaspar Winkler & Co. | (Meth) acrylic ester binders from glycolyzed aromatic polyesters |
-
2003
- 2003-07-15 JP JP2004521763A patent/JP4260742B2/en not_active Expired - Lifetime
- 2003-07-15 PT PT03764590T patent/PT1521786E/en unknown
- 2003-07-15 DE DE60320556T patent/DE60320556T2/en not_active Expired - Lifetime
- 2003-07-15 SI SI200331208T patent/SI1521786T1/en unknown
- 2003-07-15 EP EP03764590A patent/EP1521786B1/en not_active Expired - Lifetime
- 2003-07-15 AT AT03764590T patent/ATE393175T1/en active
- 2003-07-15 DK DK03764590T patent/DK1521786T3/en active
- 2003-07-15 CA CA2491319A patent/CA2491319C/en not_active Expired - Fee Related
- 2003-07-15 ES ES03764590T patent/ES2301830T3/en not_active Expired - Lifetime
- 2003-07-15 AU AU2003249203A patent/AU2003249203B2/en not_active Ceased
- 2003-07-15 US US10/619,904 patent/US6806337B2/en not_active Expired - Lifetime
- 2003-07-15 WO PCT/US2003/021902 patent/WO2004007579A1/en active Application Filing
-
2008
- 2008-05-26 CY CY20081100537T patent/CY1107961T1/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES2301830T3 (en) | 2008-07-01 |
| US20040019131A1 (en) | 2004-01-29 |
| EP1521786A1 (en) | 2005-04-13 |
| CY1107961T1 (en) | 2013-09-04 |
| AU2003249203A1 (en) | 2004-02-02 |
| ATE393175T1 (en) | 2008-05-15 |
| DE60320556D1 (en) | 2008-06-05 |
| JP2005533153A (en) | 2005-11-04 |
| PT1521786E (en) | 2008-05-27 |
| JP4260742B2 (en) | 2009-04-30 |
| US6806337B2 (en) | 2004-10-19 |
| CA2491319C (en) | 2010-02-16 |
| DE60320556T2 (en) | 2009-05-28 |
| WO2004007579A1 (en) | 2004-01-22 |
| EP1521786B1 (en) | 2008-04-23 |
| DK1521786T3 (en) | 2008-07-28 |
| AU2003249203B2 (en) | 2008-08-07 |
| SI1521786T1 (en) | 2008-08-31 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request | ||
| MKLA | Lapsed |
Effective date: 20220301 |
|
| MKLA | Lapsed |
Effective date: 20200831 |